The 5 Principles of Moonlighting Success (With Case Studies From Famous Men)

Gallup surveys have found that a majority of Americans aren’t “engaged” with their jobs, as defined as “those who are involved in, enthusiastic about and committed to their work and workplace.” Almost 18% of employees are in fact “actively disengaged” from their jobs.

Maybe you’re somewhere in that 70% of the working disconnected. Maybe you don’t positively hate your job, but you don’t find it particularly fulfilling either. You don’t feel like your work calls upon your abilities or scratches a certain itch that won’t go away.

So you think about doing something really different, and daydream about other possibilities. But the gap between where you are now and where you’d like to be seems huge. You’re not in a situation where you can just up and quit your day job. So how can you carve out an entirely new path for yourself while tethered to your 9-5?

How can you build a bridge between your life now and the life you want?

The answer is moonlighting: working a side project in your spare time until it becomes viable enough to be your full-time gig, or simply offers sufficient satisfaction that you don’t mind that your day job isn’t the end all, be all of your existence.

If you’ve ever considered moonlighting your way to a different life, today we’ll walk you through the 5 fundamental principles of doing so successfully, using short case studies from famous men in the fields of literature, science, and entrepreneurship to illustrate these keys in action.

Whether the moon’s hanging outside your window right now, or you’re reading this at the desk of your so-so job, let’s get right into it.

Moonlighting Success Principle #1: Make the Most of Your Spare Time (You’ve Got More of It Than You Think)

When you work a day (or night) job it can seem like you have little time of your own. But assuming you work for 8 hours, and sleep for 8 hours, that still leaves you with 8 hours each weekday to do whatever you’d like with. And then there are the weekends! Early mornings, late evenings, and one’s Saturdays and Sundays represent rich repositories of opportunity for those who wish to move their life in a new direction.

While most men fritter these valuable stretches of free time away, the disciplined and driven spin them into gold.

Winning the Battle as a Weekend Warrior: F. Scott Fitzgerald

When F. Scott Fitzgerald left Princeton to join the Army and serve in WWI, he continued the literary efforts he had begun as a student during his training at Fort Leavenworth, KS.

Each weekend, while his fellow soldiers went off to dances and bars in Kansas City, Fitzgerald planted himself at a table in the smoky Officer’s Club and immersed himself in writing; from 1:00 PM to midnight on Saturdays, and 6:00 AM to 6:00 PM on Sundays, he lived inside “smeary pencil pages.” After 3 months of this routine, he had completed the 120,000-word draft for what would become This Side of Paradise.

Graveyard Shift, Resurrected Dream: William Faulkner

Fellow novelist William Faulkner found a way to crank out a novel while working the night shift as supervisor of a power plant at the University of Mississippi. Having recently married a divorcee with two small children, the 32-year-old took the job to support his family.

Faulkner clocked in each day at 6 PM for a 12-hour shift. From 11 PM to 4 AM, while the world was asleep and not in need of much power, there wasn’t much to do around the plant. Amid the hum of machines, using an overturned wheelbarrow as a desk, Faulkner found he could write a whole chapter during this window of time. After his shift was over, he’d come home, eat breakfast, and then sleep for a couple of hours. In the afternoons he continued writing and took naps. Then it was back to the power plant again. By sticking to this schedule, Faulkner managed to finish As I Lay Dying in just 47 days.

Moving From Point A to Point B, Physically and Professionally: Nicholson Baker & Wallace Stevens

While mornings, nights, and weekends offer longer stretches to work on one’s side project, a moonlighter shouldn’t neglect the smaller pockets of spare time he has available either.

Modern author Nicholson Baker used the lunch breaks of his office job to scribble notes for a novel — calling this time his “pure, blissful hour of freedom.” When Baker later took a job that required a 90-minute commute, he used the drive to dictate his writing into a mini-cassette recorder.

The poet Wallace Stevens composed his verse on a commute of a different kind. Stevens enjoyed the steady income provided by a 9-5 job, and worked for the Hartford Accident and Indemnity Company for almost 40 years, not even quitting after winning the Pulitzer Prize and being offered a faculty position at Harvard. A prodigious walker from an early age who never learned to drive, Stevens fit his poetry composition in on his several mile-long strolls to and from work. He found solitude and creativity on these meditative perambulations — the scenes furnishing imagery, his cadence providing rhythm — and when inspiration struck, he’d jot down a line or two on the envelopes he kept stuffed in his pockets.

Possibilities in Spare Moments: Abraham Lincoln

Abraham Lincoln provided himself with an autodidactic education by utilizing every spare moment of his day for self-study. Not only did he read during the mornings and evenings, but he always carried a book with him as he went about his jobs as a store owner, postmaster, and surveyor; as soon as there arose a minute of downtime, he’d crack open the tome and take in a page or two. In this way, he slowly worked through a library of legal texts, became a lawyer, and entered public life.

With discipline and persistence, Lincoln literally moon- (and sun-) lighted his way to the presidency.

Takeaways From Moonlighting Success Principle #1

Even when you feel like you’re already quite busy, there are usually pockets of time you’re underutilizing that could be converted into the runway for getting a side project off the ground. Using these spare moments will certainly involve sacrifice — forgoing social engagements, leisurely smartphone-surfing lunches, and sleep — but if you want to escape the orbit of your 9-5, the effort is worth it.

Moonlighting Success Principle #2: Consistently Maximize the Time You Do Have

When you’re trying to side hustle your way to a dream, it’s not enough to set aside certain windows of time to work on your goal. What you do in that time — how you actually use it — is crucial. Do you sit down at your desk, say you’re going to start working, and then get distracted by reddit? Or do you labor diligently and consistently in order to be as productive as possible and maximize the value of your spare moments?

A man who did the latter to the nth degree was Anthony Trollope — one of the most successful, prolific, and respected English novelists of the Victorian Era.

As a 20-something he worked as a postal surveyor’s clerk in central Ireland, but what he really wanted to be was a writer. To move himself towards his goal, he began writing during the frequent train trips that were required by his job. But Trollope really hit his stride when he took a position as postal surveyor in England and moved to a home outside London.

In the 8 years he worked there before he retired from the postal service, the married moonlighter turned out 9 novels, 5 non-fiction travel books, and numerous articles and short stories, all while hunting at least twice a week, enjoying a robust social life, traveling 6 weeks out of the year for pleasure, and doing his day job “as to give the authorities of the department no slightest pretext for fault-finding.”

How did Trollope manage to balance being both a bureaucrat and an author, all while enjoying a satisfying leisure life?

By religiously sticking to a strict early morning schedule, which he describes in his autobiography:

“It was my practice to be at my table every morning at 5:30 AM; and it was also my practice to allow myself no mercy…By beginning at that hour I could complete my literary work before I dressed for breakfast.

All those I think who have lived as literary men — working daily as literary labourers — will agree with me that three hours a day will produce as much as a man ought to write. But then, he should so have trained himself that he shall be able to work continuously during those three hours — so have tutored his mind that it shall not be necessary for him to sit nibbling his pen, and gazing at the wall before him, till he shall have found the words with which he wants to express his ideas.

It had at this time become my custom — and is still my custom, though of late I have become a little lenient of myself — to write with my watch before me, and to require of myself 250 words every quarter of an hour. I have found that the 250 words have been forthcoming as regularly as my watch went. But my three hours were not devoted entirely to writing. I always began my task by reading the work of the day before, an operation which would take me half an hour, and which consisted chiefly in weighing with my ear the sound of the words and phrases…

This division of time allowed me to produce over ten pages of an ordinary novel volume a day, and if kept up through ten months, would have given as its results three novels of three volumes each in the year — the precise amount which so greatly acerbated the publisher in Paternoster Row, and which must at any rate be felt to be quite as much as the novel-readers of the world can want from the hands of one man.”

If Trollope finished a novel with time left in his early morning writing session to spare, he would simply take out a blank sheet of paper and get started on the next book.

He continued this routine even after he retired from the postal service, so that by the end of his 67-year life, he had penned 47 novels, dozens of short stories, 18 non-fiction books, and even 2 plays.

Takeaways From Moonlighting Success Principle #2

For the moonlighter, consistent, disciplined, focused work is king. Even with good concentration, it may not seem like you’re accomplishing much during the handful of hours you work on your side project each day; but the effort will add up, and ultimately reap great dividends.

Moonlighting Success Principle #3: Try to Make the Best of Your Day Job (It May Have More Advantages Than You Think)

A lot of moonlighters feel like their day jobs hold them back from doing their best work in the field they were meant to pursue; if only they could quit their 9-5, they’d finally experience a creative, innovative flourishing.

This belief has the tendency to turn into something of a self-fulfilling prophecy; having seen a light at the end of the tunnel, the disgruntled employee starts noticing the annoyances of his job even more, has less patience in putting up with them, and comes to increasingly resent his 9-5.

Yet many great men found ways not only to enjoy and appreciate their conventional jobs while they had them, but to glean things from the experience that eventually contributed to their creative side work. In fact, some actually found having a day job so beneficial, that they kept their 9-5, even after finding success in their after-hours endeavors.

The Utility of a Practical Profession: John Stuart Mill

John Stuart Mill, who many know as a philosopher and political economist, actually spent most of his adult life gainfully employed as a civil servant. When he was 17, his father got him an administrative job at the East India Company (which functioned like the State Department for the British colonies in India), and he remained there for 35 years, until the company was abolished. Mill worked each day at his office from 10am-4pm, writing dispatches to international governments and corporations.

Yet far from resenting his day job as a distraction and impediment to his “real” work as a philosopher and writer, he believed it actually did him much good.

First, he found that the time he spent grappling with practical public affairs provided him inspiration and fodder for his more abstract labors; as a critic and observer of government and society, he wasn’t throwing stones from an ivory tower, but lived right in the trenches of civil bureaucracy. He also felt that doing something different for a shift each day refreshed him to get back to his philosophical writing. Finally, in his autobiography, he describes an additional benefit: independence and freedom from the pressure to churn out books and articles aimed at making money and appealing to the masses:

“I do not know any one of the occupations by which a subsistence can now be gained, more suitable than such as this to anyone who, not being in independent circumstances, desires to devote a part of the twenty-four hours to private intellectual pursuits. Writing for the press cannot be recommended as a permanent resource to anyone qualified to accomplish anything in the higher departments of literature or thought: not only on account of the uncertainty of this means of livelihood, especially if the writer has a conscience, and will not consent to serve any opinions except his own; but also because the writings by which one can live, are not the writings which themselves live, and are never those in which the writer does his best.

Books destined to form future thinkers take too much time to write, and when written come, in general, too slowly into notice and repute, to be relied on for subsistence. Those who have to support themselves by their pen must depend on literary drudgery, or at best on writings addressed to the multitude; and can employ in the pursuits of their own choice, only such time as they can spare from those of necessity; which is generally less than the leisure allowed by office occupations, while the effect on the mind is far more enervating and fatiguing.”

In other words, if you make writing your full-time job, you’ll often have to spend the bulk of your energy doing mentally draining, superficial hackwork, instead of the things you really think are important. A day job then can thus actually free you up to work on the things you feel will have a lasting impact.

After trying unsuccessfully to cobble together an income from freelance reviewing, editing, and lecturing, T.S. Eliot took a position at Lloyds Bank in London. His more bohemian literary friends were perplexed by this move, and shook their heads at the sight of such a creative poet decked out in a conservative 3-piece suit and bowler hat, swinging an umbrella, headed off to work 8-14 hour days tabulating balance sheets. But like Mill, Eliot found that his bank job helped unleash, rather than stifle, his creativity.

Before working for the bank, the anxiety caused by his financial straits had been so great as to paralyze his writing altogether. Once he had a steady income coming in, and was freed from having to write just to make ends meet, he entered one of the most fruitful periods of his career, which included penning The Waste Land.

Eliot found that the structure and stability of his job gave him greater discipline and self-respect, as well as grist for his prose. Like Trollope, he found it easier to criticize civilization while being right in the belly of the beast; he referred to his bank job as “Sojourning among the termites.” Also like Trollope, he thought a writer could do no more than 3 hours of good work a day, and thus saw little reason in not working.

So too, there was something a little irresistible in playing the part of the conformist, decorous gentleman by day, and the imaginative, iconoclastic poet by night; camouflage can be empowering.

Day Job as the Laboratory for Future Success: Albert Einstein

Even when you do end up leaving a day job to pursue your vocation full-time, the benefits of the time you spent in the workforce can continue to contribute to your success.

After failing to find a teaching post upon graduation from Zurich Polytechnic, and spending two years living hand-to-mouth as a private tutor, Albert Einstein famously went to work as a clerk at the Federal Patent Office in Bern, Switzerland. While some have erroneously believed he merely bided his time there until he could become a full-fledged scientist, the years he spent as a patent examiner helped set the stage for the rest of his illustrious career.

The job wasn’t overly demanding and left Einstein time to work on his own scientific research after his shift (and sometimes during it — legend has it he called the drawer in his desk at work where he stashed his personal notes “the department of theoretical physics”). So too, his newfound financial stability was experienced as a welcome change. “I am doing well,” he wrote a friend. “I am an honorable federal ink pisser with a regular salary. Besides I ride my old mathematico-physical hobbyhorse and saw on my violin.” He even recommended that a friend come work at the same office, advising him to keep in mind that “Besides the eight hours of work, each day also has eight hours for mischief, and then there’s Sunday.”

Indeed, having a 9-5 at this time in Einstein’s life suited him fine; he was glad to have his independence apart from the publish-or-perish pressures that came with being attached to a university. “A practical profession is a salvation for a man of my type,” he mused. “An academic career compels a young man to scientific production, and only strong character can resist the temptation of superficial analysis.”

“Free from everyday worries to produce my best creative work,” Einstein in fact experienced an absolute intellectual flourishing during his tenure at the patent office. He completed a dissertation, earned his PhD from the University of Zurich, and published 32 papers, including 4 positively groundbreaking treatises in 1905 — which has been termed his annus mirabilis (miracle year) — alone.

Independence and income weren’t the only things about Einstein’s day job that helped propel his future career. While examining patents might not seem directly related to theories on light and space and time, his responsibility for reviewing applications related to electromagnetic devices did add fuel — some additional mental models — to the furnace of his mind, and led to his conducting new kinds of experiments.

Further, the very nature of the job sharpened his thinking; he had to utilize his visual imagination in conceptualizing how the proposed inventions would work, grasp the premises behind their mechanisms, and analyze drawings that were submitted as part of the application. He was also tasked with rewording the inventor’s description of their device, and re-formulating it in the clearest possible language. Above all, his supervisor impressed upon him the necessity of thinking critically — of not getting sucked into the inventor’s own (and possibly flawed) conclusions and rationales. In the end, Einstein said, the experience of being a patent examiner trained him to think clearly and logically — skills that would reap dividends for the rest of his life.

Einstein ultimately felt he did need more time to fully pursue his theories and left the patent office in 1909 to become an associate professor. Still, for the rest of his life he was grateful for his experience as a 9-5er and waxed nostalgic about his stint working as a patent examiner. “In this worldly cloister,” he remembered of his old office days, “I hatched my most beautiful thoughts.”

Takeaways From Moonlighting Success Principle #3

Many folks feel like their day job is an impediment to allowing their side hustles to blossom, and wish they could pursue what they feel to be their true vocation with complete single-mindedness. But what the above men (and plenty more examples could be furnished) show, is that having a full-time job can actually be quite advantageous in getting your dream off the ground — if you have the right attitude about it.

You’ll hear plenty of people say you should just quit your current job if you want to make it in another field — the reasoning being that the resulting pressure will force you to either sink or swim. And yet history shows that sometimes the very opposite is true: having a safety net can liberate you to do your very best and most creative work.

Plus, the skills and perspective you gain by working a regular job can carry over in unexpected ways and indirectly enhance your ability to perform your side hustle. Even the annoyances of a day job can be used as fodder for your artistic efforts!

That being said, the day job you choose does matter. It should be stimulating enough not to bore you, and yet undemanding enough not to sap the energies you’ll need for your “second shift.” Before Eliot’s banking gig, for example, he had tried working as a high school teacher, but found that “performing” in front of students each day left him feeling too tired to write in the evenings, or even on holiday breaks. Mill described the needed balance in a creative professional’s day job this way: “sufficiently intellectual not to be a distasteful drudgery, without being such as to cause any strain upon the mental powers of a person used to abstract thought.”

Moonlighting Success Principle #4: Be Patient and Take Things Step-by-Step

Even if you’re sure you will want to quit your job once your side business takes off, you don’t need to be in a hurry to get there.

In many a new moonlighter’s mind, they see an adequate source of income from their side hustle accruing in just a few months, and imagine themselves turning in their resignation at their office job before the new year arrives.

Not only is this expectation unreasonable in the vast majority of cases, it’s also frequently unwise.

If you go into a moonlighting endeavor with an instant gratification mindset, you’ll invariably end up quitting prematurely once immediate results are not forthcoming, and you realize just how much work and time success is going to involve. Plus, hanging on to your day job for not just a year, but maybe several, is likely going to be essential to eventually being able to switch to your side business full-time.

An Empire Can Be Slow to Develop: George Eastman

It took George Eastman, the founder of Kodak, 4 years from the time he began tinkering with and learning about the art and mechanics of photography to the day he finally quit his job as a bank clerk.

Eastman had originally gotten into taking pictures as a hobby, but quickly realized there was great commercial potential in figuring out ways to simplify what was then a bulky, messy, time-consuming process. The 23-year-old taught himself all the ins and outs of the field by studying journals, talking with local photographers, and reading chemistry manuals, then focused his efforts on improving the plates used in cameras.

At the time, “wet” plates were used, which had to be coated by hand with an emulsion and sensitized with nitrate of silver right before exposure. For two years, Eastman experimented in the laboratory he had created inside his mother’s boarding house where he lived, seeking to develop “dry” plates that were pre-coated with an emulsion, as well as a machine which could apply the coating manually, evenly, and cheaply.

Eastman patented the resulting inventions, and began to sell the rights to manufacture them to companies in Europe. All the while, he kept his job working 6 days a week as an assistant bookkeeper at the Rochester Savings Bank. The position provided a fairly handsome salary, and helped fund Eastman’s after-hours experiments. On weekdays, he’d work on his growing photography business from when he got off from the bank in the afternoon until morning the next day; his mother would often wake to find her son asleep on the floor. On the weekends, he would catch up on his sleep, and then begin his punishing schedule again on Monday.

When Eastman began manufacturing his own photographic devices, he rented a small loft above a music store two blocks from the bank. After his shift crunching numbers, he’d bike to his “factory,” put on his side hustle hat, and work through the night, stopping only for catnaps taken in a hammock he had designed himself and slung up in the corner.

Eastman initially took care of all the engineering, marketing, and bookkeeping for the business himself. He tested the market for his inventions by personally selling them to local photographers and getting their feedback. But as his business started to take off, he began to bring on more employees and moved into a larger facility.

Then, after the 27-year-old inventor and entrepreneur had spent 4 years tinkering and testing in his spare time, he formed the Eastman Dry Plate Company, and finally hung up his hat as a banker.

You Have to Crawl Before You Run: Phil Knight

The founder of Nike made an even slower and more protracted transition from bean counter to CEO.

Phil Knight had gotten the idea of selling Japanese running shoes in the U.S. while earning his MBA from Stanford, and on a post-graduation trip round the world, he stopped in Japan to put the gears of that dream in motion. Knight met with the manufacturer of Tiger-brand shoes, which he admired, and managed to secure the rights to distribute them back in the States. The manufacturer promised to ship Knight samples of the sneakers soon.

The Tigers ended up taking over a year to arrive. In the meantime, Knight enrolled in classes needed to get his CPA and took a job with the accounting firm Lybrand, Ross Bros. & Montgomery. When the shoes finally showed up, he used them to convince the University of Oregon’s track coach (who Knight had run for during his undergrad days) to partner with him, and together they formed Blue Ribbon Sports (the company that would become Nike) in 1964.

A now 26-year-old Knight got 300 more pairs of Tiger shoes shipped to him and stacked them up in the basement of his parents’ home, where he still lived. Feeling ready to make a go at being a full-time running shoe entrepreneur, he promptly quit his accounting job, loaded his sneakers in the trunk of his Plymouth Valiant, and drove all over the Pacific Northwest, showing up to track meets and talking to coaches and runners about why they needed to try Tigers.

The shoes caught on quickly. People were writing, calling, and even showing up at the door of the Knight home asking to buy a pair. Knight hired a salesman to expand his market and pitch Tigers to runners in California.

But by late 1965, Blue Ribbon Sports was in trouble. Sales were strong, but the company was also frequently in debt. With the balance sheet hovering around zero, Knight had to take out a loan each time he ordered another shipment of shoes, but his bank, which thought he was too much of a credit risk, wouldn’t extend him the needed funding.

Seeking a plan B in case Blue Ribbon went belly up, as well as another source of funding, Knight took his CPA exam, and accepted a job as an accountant at Price Waterhouse. Even though he was back to having a corporate day job, he largely didn’t mind, as he was able to invest a significant portion of his paychecks into Blue Ribbon, “padding my previous equity, [and] boosting the company’s cash balance.”

In addition to often working 6 days a week as an accountant, Knight, who had served one year of active service in the Army before joining the Reserves, also had to spend 14 hours a month doing military training. Yet these significant time constraints didn’t stymy Knight’s drive; on weekends, nights, and “vacations” he continued to expand Blue Ribbon’s footprint.

In 1966, he moved into a one-room apartment, and lined the place wall-to-wall with his entire inventory of shoes. A year later, having quickly outgrown these cramped quarters, he moved the business into a larger one-room commercial space which consisted of a retail/office area up front, and a “warehouse” in the back (the areas were separated by a jerry-rigged wall of plywood).

By 1967, Knight was managing 4 employees, two retail stores, and an office on both the West and East coasts.

And he was still working as accountant.

It’s not that Knight didn’t greatly desire to quit his day job in order to concentrate solely on his burgeoning sneaker business; as he relates in his autobiography on the early years of Nike, it just took years for that to become a viable option:

“I wanted to dedicate every minute of every day to Blue Ribbon. I’d never been a multitasker, and I didn’t see any reason to start now. I wanted to be present, always. I wanted to focus constantly on the one task that really mattered. If my life was to be all work and no play, I wanted my work to be play. I wanted to quit Price Waterhouse. Not that I hated it; it just wasn’t me.

I wanted what everyone wants. To be me, full-time.

But it wasn’t possible. Blue Ribbon simply couldn’t support me. Though the company was on track to double sales for a fifth straight year, it still couldn’t justify a salary for its cofounder.”

While Knight couldn’t get by without a day job, he did come up with a compromise for himself in 1968 — taking a job that still paid the bills, but offered more flexibility: teaching classes at Portland State University. As an assistant professor, he “still didn’t have all the time I wanted or needed for Blue Ribbon but I had more.”

Finally, in 1969, 7 years after first ordering a sample of Tiger shoes, and just shy of his 31st birthday, Knight quit teaching, and drew his first salary from Blue Ribbon.

Building a Blog: Um, Me?

Now I don’t consider myself a famous man, or equal to the ranks of the other gents we’ve talked about. But allow me to mention the time it frequently takes to make a full-time living on a blog, as it’s commonly quite underestimated.

With blogging and online media/commerce, people often think the old rules don’t apply and that you can become an overnight success. Perhaps that happens for some folks, but that wasn’t the case with my creating the Art of Manliness.

I started AoM in January of 2008 when I was in law school and working a part-time job. I’d work and study at school from 8 am to 8 pm each weekday, and then work on the site for a few hours in the evenings and the weekends. Kate supported us by teaching at a community college.

When I graduated in 2009, we were barely making enough revenue from AoM to scrape by so I took a corporate job working for a legal research company.

It wasn’t until December 2010, 3 years after I started the Art of Manliness, that I was able to make it my full-time gig. I think moonlighting during those years truly worked to my advantage. I was able to use the modest revenue generated by the site to pay off Kate and my student loans, so that I had greater financial stability when I made the jump. I got plenty of time to figure out whether blogging or working in the legal field was what I ultimately wanted to do. And I got better at being the editor-in-chief of a magazine and was able to make and learn from mistakes without the pressure of relying on the site for my livelihood.

That AoM (hopefully) comes off as a site with a lot of integrity, is partly due to the fact that while setting its course, I didn’t have to compromise my principles in order to try to maximize its profits to keep a roof over my head.

Takeaways From Moonlighting Success Principle #4

Even though you might be tempted to, you don’t necessarily need to quit your day job as soon as you get an idea for a side business. In fact, in can be beneficial to take things slow and build up your biz step-by-step, before making the leap.

Keeping your eggs in two baskets until the moonlighting embryos hatch, gives you the financial independence to make the best possible decisions, allows you to experiment, refine your ideas, and test the market for your product, provides access to a steady source of equity, and helps set the stage for a successful launch of your business.

Moonlighting allows you to be both prudent and conservative, and daring and risk-taking.

In Antifragile, philosopher Nassim Taleb calls this the barbell, or bimodal, strategy, and thinks it’s the soundest way to approach all uncertainties in life:

“I initially used the image of the barbell to describe a dual attitude of playing it safe in some areas…and taking a lot of small risks in others…hence achieving antifragility. That is extreme risk aversion on one side and extreme risk loving on the other…For antifragility is the combination aggressiveness plus paranoia—clip your downside, protect yourself from extreme harm, and let the upside…take care of itself.”

By moonlighting while keeping your day job, you minimize the downsides of your side business failing, while opening up the opportunity for it to take off into something great.

It’s a strategy that gives you optionality.

So play the long game with your side hustle; don’t feel anxious about aiming for slow and steady progress. Measure you expectations in years, rather than months. There may come a point where, like stretching out Silly Putty, you reach a breaking point and have to choose to go full-time with either your day job or side business. But the string can be stretched out a lot longer than many think, and it’s likely in your interest to keep on pulling as long as you can.

Moonlighting Success Principle #5: Don’t Make Excuses About Circumstances and Distractions — Just Get Going and Stay Going!

We’ve exploded the two most common excuses would-be moonlighters give for not getting going with a side vocation.

Think you don’t have enough time? You can find it if you look hard enough, and maximize your spare moments.

Feel like your day job’s holding you back? It’s probably the very opposite.

Yet there are almost certainly those out there, who will still find reasons to make themselves the exceptions. “Well that’s fine for these guys, but it’s not possible for me because ____.”

Maybe it’s that you think moonlighting is only for single guys, and you can’t do it because you have kids. Your current living situation and responsibilities just aren’t conducive to concentration.

Yet when Einstein was working for the patent office, he went home to a small apartment and a new wife and baby boy. A biographer describes the abode as having “many distractions…Wet clothes were strung across the kitchen drying…the room smelled of diapers and stale smoke, and puffs of smoke arose every so often from the stove.” But “these things didn’t seem to bother Einstein. He had the baby on one knee and a pad on the other, and every so often he would write an equation on the pad, then quickly rock the baby a little faster as he began to fuss.”

When Stephen King wrote his first novel, Carrie, he and his wife, who were parents to a toddler and a newborn, were just barely getting by and were living in a double-wide trailer. His wife Tabby watched the kids while he taught English at a private school, and then she went to work the second shift at Dunkin Donuts. In the summers he made extra money working as a janitor, gas station attendant, and in an industrial laundry facility.

King did his writing in the evenings, working on a makeshift desk Tabby had found room for by wedging it between the washing machine and the dryer. He hammered out his stories on a typewriter as Tabby made dinner, and his kids cried and toddled around.

So kids and an unfavorable working environment just plain don’t cut the mustard as reasons you can’t moonlight. If you wait for the perfect conditions to get started on your side project, you’ll wait forever.

But maybe it still seems just too plain hard. You’re tired after your day job, and don’t you deserve to relax and have some fun?

Well, it just depends on what you consider enjoyable, and how much satisfaction you’re really getting from your current pastimes. Working on your side hustle just might become your favorite part of the day.

Joseph Heller did his writing in the evenings after work as an advertising copywriter for magazines like Time, Look, and McCall. He wrote Catch-22 by putting in 2-3 hours each night on it for eight years. At one point, he decided to give himself a break and just spend his evenings watching television with his wife instead. But as he recalled, this kind of vegged-out relaxation didn’t suit him: “Television drove me back to Catch-22. I couldn’t imagine what Americans did at night when they weren’t writing novels.”

Of the time Phil Knight spent juggling his job at Price Waterhouse, Army Reserve training, and growing Blue Ribbon, he remembers having “No friends, no exercise, no social life.” And yet he felt “wholly content. My life was out of balance, sure, but I didn’t care. In fact, I wanted even more imbalance.”

A moonlighter who successfully fights through the common excuses, and starts and sticks with his side project, frequently finds that though the extra work makes him far busier than working a day job alone, the extra endeavor enhances rather than impoverishes his life. He has a “secret” mission to work on, plans to scheme, and an interest and purpose to dream about outside the TPS reports done in his cubicle each day. If his 9-5 is just so-so, and not wholly fulfilling, he has something else to get up early or stay up late for — a labor that just might turn out to be his real life’s work.